Electronic Supplementary Information for CrystEngComm This Journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Thomas Muthiah Packianathan' 'Gabriele Bocelli' 'P. Panneerselvam' 'Ponraj Prabakaran' 'Lara Righi' 'Balakrishnan Umadevi' _publ_contact_author_name 'Prof Packianathan Thomas Muthiah' _publ_contact_author_address ; Department of Chemistry Bharathidasan University Tiruchirappalli Tamilnadu 620024 INDIA ; _publ_contact_author_email TOMMTRICHY@YAHOO.CO.IN _publ_requested_journal 'Cryst Eng. Comm.' _publ_section_title ; Conformational Pseudo-polymorphism and Hydrogen Bonding:Benzthiazide Anhydrate and Monohydrate, An Antihypertensive Drug ; data_benzthiazide-anhydrate _database_code_depnum_ccdc_archive 'CCDC 162195' _audit_creation_method SHELXL _chemical_name_systematic ; 6-chloro-3[[(phenylmethyl)thio]ethyl]4H-1,2,4-benzthothiadiazine- 7-sulfonamide-1,1-dioxide ; _chemical_name_common benzthiazide-anhydrate _chemical_formula_moiety 'C15 H14 Cl1 N3 O4 S3' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C15 H14 Cl1 N3 O4 S3' _chemical_formula_weight 431.95 _chemical_melting_point 'not measured' _chemical_compound_source 'From LKF' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/a' _symmetry_space_group_name_Hall '-P 2yab ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 10.726(2) _cell_length_b 9.0275(13) _cell_length_c 18.333(7) _cell_angle_alpha 90.00 _cell_angle_beta 97.24(2) _cell_angle_gamma 90.00 _cell_volume 1761.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 16.1 _cell_measurement_theta_max 25.8 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.629 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 0.601 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf-Nonius CAD4' _diffrn_measurement_method 2\q/\w _diffrn_standards_number 4 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% negligible _diffrn_reflns_number 3278 _diffrn_reflns_av_R_equivalents 0.0668 _diffrn_reflns_av_sigmaI/netI 0.0205 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 25.2 _reflns_number_total 3090 _reflns_number_observed 2724 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Enraf Nonius CAD4' _computing_cell_refinement MolEN _computing_data_reduction MolEN _computing_structure_solution SIR93 _computing_structure_refinement SHELXL-97 _computing_molecular_graphics 'PLATON, A.L.Spek' _computing_publication_material 'PLATON, A.L.Spek' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.1272P)^2^+1.0413P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3090 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0640 _refine_ls_R_factor_obs 0.0589 _refine_ls_wR_factor_all 0.1701 _refine_ls_wR_factor_obs 0.1642 _refine_ls_goodness_of_fit_all 1.077 _refine_ls_goodness_of_fit_obs 1.113 _refine_ls_restrained_S_all 1.077 _refine_ls_restrained_S_obs 1.113 _refine_ls_shift/esd_max 0.101 _refine_ls_shift/esd_mean 0.007 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Cl Cl Uani 0.57027(9) 0.53379(10) 0.08261(4) 1.000 0.0463(3) . . S1 S Uani 0.87253(8) 0.23356(8) 0.35510(4) 1.000 0.0310(3) . . S2 S Uani 0.82760(8) 0.78271(8) 0.44857(4) 1.000 0.0325(3) . . S3 S Uani 0.69419(9) 0.20746(9) 0.06501(4) 1.000 0.0383(3) . . O1 O Uani 0.8019(3) 0.1133(3) 0.38027(13) 1.000 0.0480(9) . . O2 O Uani 0.9946(3) 0.1997(3) 0.33763(14) 1.000 0.0540(11) . . O3 O Uani 0.7592(3) 0.0706(3) 0.08072(13) 1.000 0.0514(9) . . O4 O Uani 0.5649(3) 0.2050(3) 0.0345(2) 1.000 0.0606(12) . . N2 N Uani 0.8838(3) 0.3624(3) 0.41740(13) 1.000 0.0332(8) . . N3 N Uani 0.7698(4) 0.2967(4) 0.0104(2) 1.000 0.0516(14) . . N4 N Uani 0.7370(2) 0.5215(3) 0.35125(14) 1.000 0.0285(8) . . C3 C Uani 0.8172(3) 0.4829(3) 0.4100(2) 1.000 0.0279(8) . . C5 C Uani 0.6559(3) 0.5116(3) 0.2241(2) 1.000 0.0290(11) . . C6 C Uani 0.6482(3) 0.4420(3) 0.1571(2) 1.000 0.0292(10) . . C7 C Uani 0.7060(3) 0.3039(3) 0.1497(2) 1.000 0.0299(9) . . C8 C Uani 0.7755(3) 0.2411(3) 0.2100(2) 1.000 0.0301(11) . . C9 C Uani 0.7845(3) 0.3125(3) 0.2778(2) 1.000 0.0256(8) . . C10 C Uani 0.7246(2) 0.4475(3) 0.2848(2) 1.000 0.0244(8) . . C11 C Uani 0.8302(3) 0.5898(3) 0.4738(2) 1.000 0.0328(10) . . C12 C Uani 0.9708(3) 0.7986(4) 0.4059(2) 1.000 0.0379(12) . . C13 C Uani 0.9637(3) 0.7415(4) 0.3288(2) 1.000 0.0331(12) . . C14 C Uani 1.0354(3) 0.6221(4) 0.3108(2) 1.000 0.0446(12) . . C15 C Uani 1.0272(4) 0.5745(5) 0.2381(3) 1.000 0.0595(14) . . C16 C Uani 0.9493(4) 0.6437(5) 0.1837(2) 1.000 0.0601(16) . . C17 C Uani 0.8761(4) 0.7607(5) 0.2008(2) 1.000 0.0524(12) . . C18 C Uani 0.8833(3) 0.8092(4) 0.2731(2) 1.000 0.0402(12) . . H1 H Uiso 0.815(3) 0.152(4) 0.2072(16) 1.000 0.022(7) . . H2 H Uiso 0.614(3) 0.606(4) 0.2280(18) 1.000 0.029(8) . . H3 H Uiso 0.706(4) 0.597(5) 0.353(2) 1.000 0.044(11) . . H4 H Uiso 0.754(3) 0.582(4) 0.499(2) 1.000 0.034(8) . . H5 H Uiso 0.902(4) 0.571(5) 0.512(2) 1.000 0.046(10) . . H6 H Uiso 1.025(3) 0.746(4) 0.437(2) 1.000 0.034(9) . . H7 H Uiso 0.979(3) 0.902(5) 0.406(2) 1.000 0.047(10) . . H8 H Uiso 1.085(4) 0.580(5) 0.347(2) 1.000 0.048(11) . . H9 H Uiso 1.072(5) 0.499(7) 0.224(3) 1.000 0.10(2) . . H10 H Uiso 0.951(4) 0.608(6) 0.137(3) 1.000 0.077(15) . . H11 H Uiso 0.806(4) 0.825(6) 0.163(3) 1.000 0.074(14) . . H12 H Uiso 0.829(3) 0.897(4) 0.285(2) 1.000 0.040(9) . . H13 H Uiso 0.851(5) 0.295(6) 0.017(3) 1.000 0.084(19) . . H14 H Uiso 0.745(5) 0.368(7) -0.005(3) 1.000 0.072(17) . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl 0.0654(6) 0.0450(5) 0.0251(4) 0.0027(3) -0.0078(4) 0.0159(4) S1 0.0486(5) 0.0223(4) 0.0214(4) 0.0014(3) 0.0016(3) 0.0090(3) S2 0.0437(5) 0.0219(4) 0.0320(5) -0.0042(3) 0.0058(3) 0.0024(3) S3 0.0611(6) 0.0295(5) 0.0228(4) -0.0060(3) -0.0004(4) 0.0014(4) O1 0.085(2) 0.0240(12) 0.0344(13) 0.0073(10) 0.0056(12) -0.0026(12) O2 0.057(2) 0.066(2) 0.0383(14) -0.0036(12) 0.0030(12) 0.0277(14) O3 0.092(2) 0.0296(13) 0.0310(13) -0.0056(10) 0.0011(12) 0.0095(13) O4 0.066(2) 0.062(2) 0.049(2) -0.0187(14) -0.0118(13) -0.0060(14) N2 0.0507(15) 0.0249(13) 0.0226(12) -0.0005(10) -0.0008(11) 0.0072(12) N3 0.080(3) 0.046(2) 0.031(2) 0.0055(14) 0.016(2) 0.010(2) N4 0.0374(14) 0.0222(13) 0.0254(13) -0.0025(10) 0.0025(10) 0.0074(11) C3 0.0384(15) 0.0246(15) 0.0207(14) 0.0030(11) 0.0040(11) -0.0015(12) C5 0.0337(15) 0.025(2) 0.028(2) -0.0010(12) 0.0024(12) 0.0034(12) C6 0.0348(15) 0.029(2) 0.0223(14) 0.0034(12) -0.0026(11) 0.0009(12) C7 0.041(2) 0.0258(14) 0.0228(14) -0.0017(11) 0.0034(12) -0.0026(12) C8 0.042(2) 0.0203(14) 0.028(2) 0.0010(11) 0.0046(13) 0.0010(13) C9 0.0342(14) 0.0220(14) 0.0203(13) 0.0015(11) 0.0023(11) -0.0005(12) C10 0.0268(13) 0.0221(14) 0.0243(14) 0.0000(11) 0.0031(11) 0.0001(11) C11 0.052(2) 0.0221(15) 0.0237(15) -0.0017(12) 0.0020(14) -0.0005(13) C12 0.041(2) 0.033(2) 0.039(2) 0.0022(15) 0.0026(15) -0.0044(15) C13 0.032(2) 0.030(2) 0.038(2) 0.0036(13) 0.0077(13) -0.0054(13) C14 0.043(2) 0.039(2) 0.053(2) 0.003(2) 0.011(2) 0.001(2) C15 0.062(2) 0.049(2) 0.072(3) -0.019(2) 0.026(2) -0.006(2) C16 0.071(3) 0.068(3) 0.045(2) -0.015(2) 0.022(2) -0.025(2) C17 0.060(2) 0.057(2) 0.040(2) 0.006(2) 0.005(2) -0.018(2) C18 0.043(2) 0.036(2) 0.042(2) 0.0063(15) 0.0068(14) -0.0026(15) _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl C6 1.721(4) . . yes S1 O1 1.433(3) . . yes S1 O2 1.420(3) . . yes S1 N2 1.624(3) . . yes S1 C9 1.752(4) . . yes S2 C11 1.801(3) . . yes S2 C12 1.815(4) . . yes S3 O3 1.430(3) . . yes S3 O4 1.429(3) . . yes S3 N3 1.586(4) . . yes S3 C7 1.771(4) . . yes N2 C3 1.299(4) . . yes N4 C3 1.337(4) . . yes N4 C10 1.381(4) . . yes N3 H14 0.74(6) . . no N3 H13 0.86(5) . . no N4 H3 0.76(4) . . no C3 C11 1.509(5) . . no C5 C6 1.373(5) . . no C5 C10 1.382(5) . . no C6 C7 1.407(4) . . no C7 C8 1.375(5) . . no C8 C9 1.393(5) . . no C9 C10 1.391(4) . . no C12 C13 1.497(5) . . no C13 C18 1.392(5) . . no C13 C14 1.388(5) . . no C14 C15 1.393(7) . . no C15 C16 1.369(6) . . no C16 C17 1.376(6) . . no C17 C18 1.389(5) . . no C5 H2 0.97(4) . . no C8 H1 0.91(4) . . no C11 H4 0.99(3) . . no C11 H5 0.99(4) . . no C12 H6 0.90(4) . . no C12 H7 0.94(5) . . no C14 H8 0.88(4) . . no C15 H9 0.89(6) . . no C16 H10 0.92(5) . . no C17 H11 1.12(5) . . no C18 H12 1.02(4) . . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O2 116.71(17) . . . yes O1 S1 N2 108.16(15) . . . yes O1 S1 C9 108.40(16) . . . yes O2 S1 N2 108.89(17) . . . yes O2 S1 C9 108.87(16) . . . yes N2 S1 C9 105.21(14) . . . yes C11 S2 C12 101.57(16) . . . yes O3 S3 O4 119.34(17) . . . yes O3 S3 N3 106.91(19) . . . yes O3 S3 C7 105.61(15) . . . yes O4 S3 N3 108.0(2) . . . yes O4 S3 C7 108.04(18) . . . yes N3 S3 C7 108.55(17) . . . yes S1 N2 C3 122.4(2) . . . yes C3 N4 C10 124.4(3) . . . yes H13 N3 H14 112(6) . . . no S3 N3 H13 119(4) . . . no S3 N3 H14 120(4) . . . no C3 N4 H3 116(3) . . . no C10 N4 H3 119(3) . . . no N4 C3 C11 116.4(3) . . . yes N2 C3 N4 126.3(3) . . . yes N2 C3 C11 117.3(3) . . . yes C6 C5 C10 119.7(3) . . . no Cl C6 C5 117.3(2) . . . yes C5 C6 C7 121.0(3) . . . no Cl C6 C7 121.7(3) . . . yes S3 C7 C6 122.5(3) . . . yes C6 C7 C8 119.3(3) . . . no S3 C7 C8 118.3(2) . . . yes C7 C8 C9 119.8(3) . . . no S1 C9 C8 120.2(2) . . . yes S1 C9 C10 119.3(3) . . . yes C8 C9 C10 120.5(3) . . . no N4 C10 C5 119.4(3) . . . yes C5 C10 C9 119.9(3) . . . no N4 C10 C9 120.7(3) . . . yes S2 C11 C3 115.0(2) . . . yes S2 C12 C13 115.8(2) . . . yes C12 C13 C14 121.9(3) . . . no C14 C13 C18 118.5(3) . . . no C12 C13 C18 119.6(3) . . . no C13 C14 C15 119.8(3) . . . no C14 C15 C16 121.1(4) . . . no C15 C16 C17 119.9(4) . . . no C16 C17 C18 119.7(4) . . . no C13 C18 C17 121.1(3) . . . no C6 C5 H2 120(2) . . . no C10 C5 H2 121(2) . . . no C7 C8 H1 121.7(19) . . . no C9 C8 H1 118.5(19) . . . no S2 C11 H4 102(2) . . . no S2 C11 H5 110(3) . . . no C3 C11 H4 108(2) . . . no C3 C11 H5 115(2) . . . no H4 C11 H5 106(3) . . . no S2 C12 H6 102(2) . . . no S2 C12 H7 99(2) . . . no C13 C12 H6 112(2) . . . no C13 C12 H7 110(2) . . . no H6 C12 H7 118(3) . . . no C13 C14 H8 117(3) . . . no C15 C14 H8 123(3) . . . no C14 C15 H9 123(4) . . . no C16 C15 H9 116(4) . . . no C15 C16 H10 116(3) . . . no C17 C16 H10 124(3) . . . no C16 C17 H11 128(3) . . . no C18 C17 H11 112(3) . . . no C13 C18 H12 120(2) . . . no C17 C18 H12 119(2) . . . no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 S1 N2 C3 -104.1(3) . . . . no O2 S1 N2 C3 128.2(3) . . . . no C9 S1 N2 C3 11.6(3) . . . . no O1 S1 C9 C8 -75.7(3) . . . . no O1 S1 C9 C10 104.7(3) . . . . no O2 S1 C9 C8 52.2(3) . . . . no O2 S1 C9 C10 -127.4(3) . . . . no N2 S1 C9 C8 168.8(3) . . . . no N2 S1 C9 C10 -10.8(3) . . . . no C12 S2 C11 C3 -65.6(3) . . . . no C11 S2 C12 C13 78.2(3) . . . . no O3 S3 C7 C6 -177.2(3) . . . . no O3 S3 C7 C8 3.5(3) . . . . no O4 S3 C7 C6 -48.4(3) . . . . no O4 S3 C7 C8 132.2(3) . . . . no N3 S3 C7 C6 68.5(3) . . . . no N3 S3 C7 C8 -110.9(3) . . . . no S1 N2 C3 N4 -3.3(5) . . . . no S1 N2 C3 C11 176.2(2) . . . . no C10 N4 C3 N2 -9.0(5) . . . . no C3 N4 C10 C5 -168.4(3) . . . . no C3 N4 C10 C9 9.0(4) . . . . no C10 N4 C3 C11 171.5(3) . . . . no N4 C3 C11 S2 -38.6(4) . . . . no N2 C3 C11 S2 141.8(3) . . . . no C10 C5 C6 C7 2.0(5) . . . . no C10 C5 C6 Cl -175.7(2) . . . . no C6 C5 C10 C9 -0.6(4) . . . . no C6 C5 C10 N4 176.9(3) . . . . no Cl C6 C7 S3 -4.5(4) . . . . no C5 C6 C7 C8 -2.7(5) . . . . no Cl C6 C7 C8 174.8(3) . . . . no C5 C6 C7 S3 177.9(3) . . . . no S3 C7 C8 C9 -178.6(2) . . . . no C6 C7 C8 C9 2.0(5) . . . . no C7 C8 C9 S1 179.9(2) . . . . no C7 C8 C9 C10 -0.6(5) . . . . no S1 C9 C10 C5 179.4(2) . . . . no S1 C9 C10 N4 2.0(4) . . . . no C8 C9 C10 N4 -177.6(3) . . . . no C8 C9 C10 C5 -0.2(4) . . . . no S2 C12 C13 C18 64.0(4) . . . . no S2 C12 C13 C14 -116.1(3) . . . . no C12 C13 C18 C17 178.8(3) . . . . no C12 C13 C14 C15 -178.9(3) . . . . no C18 C13 C14 C15 1.1(5) . . . . no C14 C13 C18 C17 -1.1(5) . . . . no C13 C14 C15 C16 0.0(6) . . . . no C14 C15 C16 C17 -1.1(7) . . . . no C15 C16 C17 C18 1.0(7) . . . . no C16 C17 C18 C13 0.1(6) . . . . no _diffrn_reflns_theta_full 25.2 _diffrn_measured_fraction_theta_max 1.0 _diffrn_measured_fraction_theta_full 1.0 _refine_diff_density_max 0.652 _refine_diff_density_min -0.584 _refine_diff_density_rms 0.113 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # #D H A D - H H...A D...A D - H...A symm(A) # N4 H3 S2 0.76(4) 2.65(4) 3.042(3) 114(3) . yes N3 H13 O4 0.86(5) 2.28(5) 3.140(6) 179(5) 4_555 yes N3 H14 O3 0.74(6) 2.29(6) 2.978(5) 155(6) 2_655 yes ############### END ############################## data_benzthiazide-monohydrate _database_code_depnum_ccdc_archive 'CCDC 162196' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6-chloro-3[[(phenylmethyl)thio]ethyl]4H-1,2,4-benzthothiadiazine- 7-sulfonamide-1,1-dioxide monohydrate ; _chemical_name_common benzthiazide-monohydrate _chemical_formula_moiety 'C15 H16 Cl1 N3 O5 S3' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C15 H16 Cl1 N3 O5 S3' _chemical_formula_weight 449.96 _chemical_absolute_configuration . _chemical_melting_point 'not measured' _chemical_compound_source 'From LKF' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.243(2) _cell_length_b 4.905(2) _cell_length_c 31.957(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.34(3) _cell_angle_gamma 90.00 _cell_volume 1907.3(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 3.51 _cell_measurement_theta_max 63.4 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.567 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 5.148 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4668 _exptl_absorpt_correction_T_max 0.7312 _exptl_absorpt_process_details DIFABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Enraf-Nonius CAD4' _diffrn_measurement_method 2\q/\w _diffrn_standards_number 4 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% negligible _diffrn_reflns_number 4093 _diffrn_reflns_av_R_equivalents 0.0424 _diffrn_reflns_av_sigmaI/netI 0.2161 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 3.63 _diffrn_reflns_theta_max 69.98 _reflns_number_total 4035 _reflns_number_gt 2201 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Enraf Nonius CAD4' _computing_cell_refinement MolEN _computing_data_reduction MolEN _computing_structure_solution SIR93 _computing_structure_refinement SHELXL-97 _computing_molecular_graphics 'PLATON, A.L.Spek' _computing_publication_material 'PLATON, A.L.Spek' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0731P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(4) _refine_ls_number_reflns 4035 _refine_ls_number_parameters 499 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1084 _refine_ls_R_factor_gt 0.0550 _refine_ls_wR_factor_ref 0.1443 _refine_ls_wR_factor_gt 0.1239 _refine_ls_goodness_of_fit_ref 0.883 _refine_ls_restrained_S_all 0.883 _refine_ls_shift/su_max 0.018 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1A Cl 0.53917(19) -0.1244(7) 0.38218(7) 0.0475(8) Uani 1 1 d . . . S1A S 0.74831(19) 0.6896(6) 0.26401(7) 0.0378(7) Uani 1 1 d . . . S2A S 0.4164(2) 0.5158(7) 0.15795(8) 0.0681(9) Uani 1 1 d . . . S3A S 0.7769(2) 0.1752(6) 0.41634(7) 0.0371(7) Uani 1 1 d . . . O1A O 0.8087(5) 0.9095(18) 0.28459(19) 0.050(2) Uani 1 1 d . . . O2A O 0.8100(5) 0.5156(18) 0.23881(18) 0.049(2) Uani 1 1 d . . . O3A O 0.8812(4) 0.3124(16) 0.41438(17) 0.043(2) Uani 1 1 d . . . O4A O 0.7752(5) -0.1094(16) 0.4247(2) 0.049(2) Uani 1 1 d . . . N2A N 0.6465(6) 0.8094(19) 0.2329(2) 0.040(2) Uani 1 1 d . . . N3A N 0.7142(6) 0.331(2) 0.45026(19) 0.046(3) Uani 1 1 d . . . H3A H 0.7400 0.3540 0.4796 0.050 Uiso 1 1 d . . . H3A' H 0.6503 0.2757 0.4572 0.054 Uiso 1 1 d . . . C3A C 0.5525(8) 0.674(3) 0.2285(3) 0.041(3) Uani 1 1 d . . . N4A N 0.5239(6) 0.472(2) 0.2521(2) 0.046(3) Uani 1 1 d . . . H4A H 0.4687 0.3081 0.2415 0.046 Uiso 1 1 d . . . C5A C 0.5420(8) 0.187(3) 0.3141(2) 0.037(3) Uani 1 1 d . . . H5A H 0.4740 0.1089 0.3056 0.06(3) Uiso 1 1 calc R . . C6A C 0.5995(7) 0.112(2) 0.3520(2) 0.033(3) Uani 1 1 d . . . C7A C 0.7017(7) 0.242(2) 0.3658(2) 0.032(3) Uani 1 1 d . . . C8A C 0.7453(7) 0.422(3) 0.3396(3) 0.039(3) Uani 1 1 d . . . H8A H 0.8141 0.4963 0.3480 0.05(3) Uiso 1 1 calc R . . C9A C 0.6902(7) 0.498(2) 0.3008(3) 0.034(3) Uani 1 1 d . . . C10A C 0.5857(7) 0.379(2) 0.2890(3) 0.034(2) Uani 1 1 d . . . C11A C 0.4645(8) 0.783(3) 0.1938(3) 0.048(3) Uani 1 1 d . . . H111 H 0.4958 0.9283 0.1784 0.14(6) Uiso 1 1 calc R . . H112 H 0.4031 0.8569 0.2069 0.11(5) Uiso 1 1 calc R . . C12A C 0.5411(12) 0.445(3) 0.1337(4) 0.086(4) Uani 1 1 d . . . H121 H 0.6007 0.4149 0.1558 0.18(8) Uiso 1 1 calc R . . H122 H 0.5306 0.2770 0.1177 0.15(6) Uiso 1 1 calc R . . C13A C 0.5749(10) 0.662(3) 0.1053(3) 0.067(3) Uani 1 1 d . . . C14A C 0.6811(12) 0.784(4) 0.1101(4) 0.089(5) Uani 1 1 d . . . H14A H 0.7304 0.7332 0.1330 0.12(6) Uiso 1 1 calc R . . C15A C 0.7131(13) 0.969(4) 0.0832(5) 0.098(5) Uani 1 1 d . . . H15A H 0.7852 1.0317 0.0871 0.15(7) Uiso 1 1 calc R . . C16A C 0.6416(12) 1.073(3) 0.0489(4) 0.087(4) Uani 1 1 d . . . H16A H 0.6624 1.2076 0.0308 0.5(3) Uiso 1 1 calc R . . C17A C 0.5375(12) 0.956(3) 0.0449(4) 0.081(4) Uani 1 1 d . . . H17A H 0.4868 1.0143 0.0229 0.08(4) Uiso 1 1 calc R . . C18A C 0.5052(11) 0.761(3) 0.0717(3) 0.069(3) Uani 1 1 d . . . H18A H 0.4340 0.6922 0.0670 0.14(6) Uiso 1 1 calc R . . Cl1B Cl 0.04097(19) 0.8699(7) 0.38467(7) 0.0481(7) Uani 1 1 d . . . S1B S 0.24520(19) 0.0408(6) 0.26794(7) 0.0381(7) Uani 1 1 d . . . S2B S -0.0008(2) 0.1358(7) 0.14657(7) 0.0628(8) Uani 1 1 d . . . S3B S 0.2785(2) 0.5641(6) 0.41901(8) 0.0386(7) Uani 1 1 d . . . O1B O 0.3048(5) -0.1844(17) 0.28915(19) 0.050(2) Uani 1 1 d . . . O2B O 0.3087(4) 0.2153(17) 0.24246(17) 0.046(2) Uani 1 1 d . . . O3B O 0.3834(5) 0.4363(16) 0.41704(17) 0.044(2) Uani 1 1 d . . . O4B O 0.2770(5) 0.8546(18) 0.4271(2) 0.054(2) Uani 1 1 d . . . N3B N 0.2186(6) 0.417(2) 0.4538(2) 0.049(2) Uani 1 1 d . . . H3C H 0.1800 0.4966 0.4704 0.050 Uiso 1 1 d . . . H3D H 0.2200 0.2536 0.4575 0.050 Uiso 1 1 d . . . N2B N 0.1418(6) -0.077(2) 0.2372(2) 0.045(2) Uani 1 1 d . . . C3B C 0.0492(8) 0.067(3) 0.2318(3) 0.045(3) Uani 1 1 d . . . N4B N 0.0244(6) 0.289(2) 0.2543(2) 0.042(2) Uani 1 1 d . . . H4B H -0.0374 0.2485 0.2550 0.075 Uiso 1 1 d . . . C5B C 0.0443(7) 0.555(3) 0.3176(2) 0.037(3) Uani 1 1 d . . . H5B H -0.0227 0.6386 0.3090 0.07(3) Uiso 1 1 calc R . . C6B C 0.1002(7) 0.625(3) 0.3553(3) 0.042(3) Uani 1 1 d . . . C7B C 0.2031(7) 0.502(2) 0.3694(3) 0.035(3) Uani 1 1 d . . . C8B C 0.2438(7) 0.308(2) 0.3424(3) 0.035(3) Uani 1 1 d . . . H8B H 0.3096 0.2193 0.3508 0.02(2) Uiso 1 1 calc R . . C9B C 0.1872(7) 0.250(2) 0.3039(2) 0.034(3) Uani 1 1 d . . . C10B C 0.0859(7) 0.362(3) 0.2918(3) 0.038(3) Uani 1 1 d . . . C11B C -0.0322(7) -0.011(3) 0.1954(2) 0.054(3) Uani 1 1 d . . . H11A H -0.1048 0.0492 0.2010 0.07(3) Uiso 1 1 calc R . . H11B H -0.0339 -0.2076 0.1928 0.03(3) Uiso 1 1 calc R . . C12B C 0.1176(10) -0.071(4) 0.1356(3) 0.086(4) Uani 1 1 d . . . H12C H 0.1815 -0.0232 0.1549 0.15(7) Uiso 1 1 calc R . . H12D H 0.1020 -0.2627 0.1390 0.10(5) Uiso 1 1 calc R . . C13B C 0.1392(9) -0.014(3) 0.0909(3) 0.065(3) Uani 1 1 d . . . C14B C 0.2133(10) 0.166(4) 0.0802(4) 0.103(6) Uani 1 1 d . . . H14B H 0.2523 0.2673 0.1016 0.07(4) Uiso 1 1 calc R . . C15B C 0.2356(12) 0.212(4) 0.0390(5) 0.108(6) Uani 1 1 d . . . H15B H 0.2856 0.3446 0.0329 0.16(7) Uiso 1 1 calc R . . C16B C 0.1834(12) 0.059(4) 0.0084(4) 0.097(5) Uani 1 1 d . . . H16B H 0.1988 0.0821 -0.0193 0.06(3) Uiso 1 1 calc R . . C17B C 0.1079(14) -0.129(4) 0.0175(5) 0.118(6) Uani 1 1 d . . . H17B H 0.0712 -0.2327 -0.0040 0.15(7) Uiso 1 1 calc R . . C18B C 0.0857(12) -0.166(4) 0.0586(4) 0.099(5) Uani 1 1 d . . . H18B H 0.0341 -0.2957 0.0646 0.09(5) Uiso 1 1 calc R . . O1WA O 0.5095(5) 0.1217(18) 0.48066(17) 0.058(2) Uiso 1 1 d . . . H1WA H 0.5000 -0.0494 0.4864 0.050 Uiso 1 1 d . . . H2WA H 0.5000 0.0946 0.4572 0.050 Uiso 1 1 d . . . O1WB O 0.0094(5) 0.6028(19) 0.48078(17) 0.061(2) Uiso 1 1 d . . . H1WB H 0.0000 0.7542 0.4814 0.050 Uiso 1 1 d . . . H2WB H -0.0400 0.5407 0.4583 0.050 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1A 0.0470(15) 0.051(2) 0.0468(13) 0.0064(15) 0.0131(11) -0.0090(16) S1A 0.0367(14) 0.0389(18) 0.0390(13) 0.0056(14) 0.0084(10) 0.0012(15) S2A 0.0765(18) 0.079(2) 0.0461(13) 0.0087(16) -0.0052(12) -0.0221(19) S3A 0.0419(16) 0.0346(19) 0.0348(12) 0.0007(14) 0.0046(11) 0.0005(17) O1A 0.050(4) 0.046(5) 0.054(4) 0.000(4) 0.006(3) -0.011(4) O2A 0.045(4) 0.054(5) 0.051(4) 0.000(5) 0.015(3) -0.003(5) O3A 0.035(4) 0.043(5) 0.049(4) -0.001(4) 0.000(3) -0.006(4) O4A 0.053(5) 0.023(5) 0.070(5) 0.007(4) 0.006(4) 0.001(4) N2A 0.045(5) 0.036(6) 0.039(4) 0.017(4) -0.001(4) 0.001(5) N3A 0.051(5) 0.067(8) 0.021(3) 0.001(5) 0.008(3) -0.002(6) C3A 0.043(6) 0.047(8) 0.031(4) 0.002(6) 0.000(4) 0.009(7) N4A 0.042(5) 0.055(7) 0.042(4) 0.015(5) 0.003(4) -0.006(5) C5A 0.037(6) 0.043(8) 0.032(4) 0.000(6) 0.009(4) -0.012(6) C6A 0.042(5) 0.025(7) 0.036(5) -0.005(5) 0.018(4) -0.001(5) C7A 0.036(5) 0.038(7) 0.023(4) 0.003(5) 0.003(4) 0.006(6) C8A 0.033(6) 0.046(8) 0.040(5) 0.003(6) 0.013(4) 0.003(6) C9A 0.027(5) 0.037(7) 0.039(5) 0.007(5) 0.011(4) -0.002(6) C10A 0.042(6) 0.031(6) 0.030(5) -0.005(5) 0.004(4) -0.004(6) C11A 0.052(6) 0.057(9) 0.035(5) 0.004(6) 0.004(5) 0.016(7) C12A 0.150(13) 0.055(9) 0.059(7) -0.005(7) 0.039(9) 0.032(9) C13A 0.086(8) 0.071(9) 0.045(6) -0.003(7) 0.014(6) 0.015(8) C14A 0.084(10) 0.102(13) 0.080(9) -0.017(10) 0.003(9) 0.009(10) C15A 0.084(11) 0.098(13) 0.118(13) -0.003(11) 0.037(9) 0.000(10) C16A 0.108(11) 0.077(11) 0.081(9) -0.013(9) 0.036(8) -0.002(10) C17A 0.113(11) 0.072(10) 0.056(7) 0.000(7) 0.006(8) -0.014(9) C18A 0.094(9) 0.065(8) 0.050(6) -0.008(6) 0.009(6) -0.020(8) Cl1B 0.0480(15) 0.049(2) 0.0493(13) -0.0082(15) 0.0155(11) 0.0074(16) S1B 0.0353(14) 0.0407(19) 0.0398(12) -0.0033(14) 0.0105(10) -0.0037(16) S2B 0.0619(16) 0.081(2) 0.0446(13) 0.0053(16) 0.0037(11) 0.0019(17) S3B 0.0418(16) 0.037(2) 0.0367(12) -0.0038(14) 0.0048(11) -0.0015(16) O1B 0.047(4) 0.049(6) 0.054(4) -0.006(4) 0.003(3) 0.007(4) O2B 0.039(4) 0.052(5) 0.051(4) -0.004(4) 0.022(3) -0.018(4) O3B 0.038(4) 0.042(6) 0.053(4) -0.004(4) 0.005(3) -0.003(4) O4B 0.057(5) 0.051(6) 0.052(4) -0.001(5) -0.006(4) -0.010(5) N3B 0.075(6) 0.036(6) 0.039(4) 0.002(5) 0.021(4) 0.002(6) N2B 0.036(4) 0.048(7) 0.052(5) -0.012(5) 0.002(4) -0.005(5) C3B 0.039(6) 0.061(9) 0.037(5) -0.003(7) 0.013(4) -0.009(7) N4B 0.035(5) 0.050(7) 0.044(4) 0.001(5) 0.010(4) -0.001(5) C5B 0.025(5) 0.046(8) 0.040(5) -0.004(6) 0.005(4) 0.001(6) C6B 0.041(6) 0.050(9) 0.037(5) -0.012(6) 0.016(4) 0.004(6) C7B 0.029(5) 0.040(7) 0.036(5) 0.007(6) 0.003(4) 0.001(6) C8B 0.034(6) 0.032(7) 0.039(5) 0.005(5) 0.005(4) 0.009(5) C9B 0.037(5) 0.037(7) 0.029(4) -0.003(5) 0.007(4) 0.000(6) C10B 0.036(6) 0.051(8) 0.028(4) -0.002(6) 0.011(4) -0.001(6) C11B 0.048(7) 0.067(10) 0.046(6) -0.011(7) -0.002(5) -0.012(7) C12B 0.089(9) 0.103(14) 0.071(8) 0.004(9) 0.025(8) 0.027(9) C13B 0.065(7) 0.088(10) 0.042(6) 0.007(7) 0.007(5) 0.009(8) C14B 0.086(9) 0.151(16) 0.073(8) -0.030(11) 0.009(7) -0.040(12) C15B 0.080(9) 0.135(16) 0.116(12) 0.007(13) 0.041(9) -0.020(12) C16B 0.110(12) 0.108(14) 0.079(9) 0.014(10) 0.041(9) 0.032(11) C17B 0.169(16) 0.112(14) 0.073(10) -0.025(11) 0.013(11) -0.007(14) C18B 0.123(12) 0.111(14) 0.066(8) 0.002(10) 0.023(8) -0.035(12) _geom_special_details ; Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1A C6A 1.726(9) . . yes Cl1B C6B 1.732(12) . . yes S1A O2A 1.443(8) . . yes S1A N2A 1.617(8) . . yes S1A O1A 1.427(8) . . yes S1A C9A 1.719(10) . . yes S2A C12A 1.820(15) . . yes S2A C11A 1.797(13) . . yes S3A O3A 1.451(6) . . yes S3A N3A 1.591(8) . . yes S3A C7A 1.799(7) . . yes S3A O4A 1.422(8) . . yes S1B O1B 1.450(8) . . yes S1B O2B 1.463(7) . . yes S1B N2B 1.621(8) . . yes S1B C9B 1.749(9) . . yes S2B C11B 1.798(9) . . yes S2B C12B 1.835(15) . . yes S3B O3B 1.437(7) . . yes S3B O4B 1.449(9) . . yes S3B N3B 1.573(8) . . yes S3B C7B 1.771(10) . . yes O1WA H2WA 0.7576 . . no O1WA H1WA 0.8696 . . no O1WB H2WB 0.9374 . . no O1WB H1WB 0.7521 . . no N2A C3A 1.323(14) . . yes N4A C3A 1.316(15) . . yes N4A C10A 1.405(12) . . yes N3A H3A 0.9624 . . no N3A H3A' 0.8793 . . no N4A H4A 1.0804 . . no N2B C3B 1.331(14) . . yes N4B C3B 1.358(16) . . yes N4B C10B 1.390(12) . . yes N3B H3D 0.8101 . . no N3B H3C 0.8441 . . no N4B H4B 0.7850 . . no C3A C11A 1.553(15) . . no C5A C10A 1.383(15) . . no C5A C6A 1.382(11) . . no C6A C7A 1.430(12) . . no C7A C8A 1.365(15) . . no C8A C9A 1.395(14) . . no C9A C10A 1.419(13) . . no C12A C13A 1.487(19) . . no C13A C18A 1.384(16) . . no C13A C14A 1.42(2) . . no C14A C15A 1.34(2) . . no C15A C16A 1.42(2) . . no C16A C17A 1.39(2) . . no C17A C18A 1.371(19) . . no C5A H5A 0.9293 . . no C8A H8A 0.9298 . . no C11A H112 0.9702 . . no C11A H111 0.9688 . . no C12A H122 0.9708 . . no C12A H121 0.9691 . . no C14A H14A 0.9297 . . no C15A H15A 0.9301 . . no C16A H16A 0.9316 . . no C17A H17A 0.9300 . . no C18A H18A 0.9313 . . no C3B C11B 1.496(13) . . no C5B C10B 1.389(17) . . no C5B C6B 1.362(12) . . no C6B C7B 1.424(14) . . no C7B C8B 1.412(13) . . no C8B C9B 1.374(12) . . no C9B C10B 1.372(13) . . no C12B C13B 1.507(14) . . no C13B C18B 1.379(19) . . no C13B C14B 1.34(2) . . no C14B C15B 1.39(2) . . no C15B C16B 1.34(2) . . no C16B C17B 1.36(3) . . no C17B C18B 1.38(2) . . no C5B H5B 0.9310 . . no C8B H8B 0.9287 . . no C11B H11A 0.9718 . . no C11B H11B 0.9679 . . no C12B H12C 0.9700 . . no C12B H12D 0.9680 . . no C14B H14B 0.9330 . . no C15B H15B 0.9285 . . no C16B H16B 0.9321 . . no C17B H17B 0.9298 . . no C18B H18B 0.9313 . . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1A S1A O2A 115.3(4) . . . yes O1A S1A N2A 109.5(5) . . . yes O1A S1A C9A 109.3(4) . . . yes O2A S1A N2A 106.7(4) . . . yes O2A S1A C9A 109.9(5) . . . yes N2A S1A C9A 105.7(4) . . . yes C11A S2A C12A 100.3(6) . . . yes O3A S3A O4A 119.7(4) . . . yes O3A S3A N3A 107.4(4) . . . yes O3A S3A C7A 104.0(4) . . . yes O4A S3A N3A 109.0(4) . . . yes O4A S3A C7A 109.3(4) . . . yes N3A S3A C7A 106.7(4) . . . yes N2B S1B C9B 105.1(4) . . . yes O2B S1B C9B 107.6(5) . . . yes O1B S1B O2B 115.8(4) . . . yes O1B S1B N2B 109.3(5) . . . yes O1B S1B C9B 111.1(4) . . . yes O2B S1B N2B 107.4(4) . . . yes C11B S2B C12B 101.2(6) . . . yes O3B S3B N3B 108.6(4) . . . yes O3B S3B C7B 105.4(4) . . . yes O3B S3B O4B 117.8(4) . . . yes O4B S3B C7B 108.3(4) . . . yes N3B S3B C7B 108.4(4) . . . yes O4B S3B N3B 108.0(5) . . . yes H1WA O1WA H2WA 91.71 . . . no H1WB O1WB H2WB 104.68 . . . no S1A N2A C3A 119.1(8) . . . yes C3A N4A C10A 125.0(8) . . . yes H3A' N3A H3A 89.76 . . . no S3A N3A H3A' 122.23 . . . no S3A N3A H3A 126.08 . . . no C10A N4A H4A 106.37 . . . no C3A N4A H4A 125.27 . . . no S1B N2B C3B 119.1(8) . . . yes C3B N4B C10B 122.1(9) . . . yes S3B N3B H3C 124.68 . . . no H3C N3B H3D 111.73 . . . no S3B N3B H3D 123.57 . . . no C3B N4B H4B 94.86 . . . no C10B N4B H4B 118.21 . . . no N2A C3A C11A 115.5(11) . . . yes N4A C3A C11A 117.4(9) . . . yes N2A C3A N4A 126.9(9) . . . yes C6A C5A C10A 119.8(9) . . . no Cl1A C6A C7A 122.8(5) . . . yes Cl1A C6A C5A 117.4(7) . . . yes C5A C6A C7A 119.7(8) . . . no S3A C7A C8A 118.2(7) . . . yes S3A C7A C6A 122.6(6) . . . yes C6A C7A C8A 119.2(7) . . . no C7A C8A C9A 122.3(9) . . . no C8A C9A C10A 117.4(9) . . . no S1A C9A C10A 118.2(7) . . . yes S1A C9A C8A 123.9(7) . . . yes C5A C10A C9A 121.4(9) . . . no N4A C10A C5A 120.1(8) . . . yes N4A C10A C9A 118.4(8) . . . yes S2A C11A C3A 110.9(10) . . . yes S2A C12A C13A 115.2(10) . . . yes C14A C13A C18A 114.4(12) . . . no C12A C13A C18A 122.4(12) . . . no C12A C13A C14A 123.2(11) . . . no C13A C14A C15A 123.0(13) . . . no C14A C15A C16A 122.7(15) . . . no C15A C16A C17A 113.8(13) . . . no C16A C17A C18A 123.7(13) . . . no C13A C18A C17A 122.3(13) . . . no C10A C5A H5A 120.18 . . . no C6A C5A H5A 119.98 . . . no C9A C8A H8A 119.05 . . . no C7A C8A H8A 118.65 . . . no H111 C11A H112 108.25 . . . no C3A C11A H112 109.27 . . . no C3A C11A H111 109.50 . . . no S2A C11A H111 109.44 . . . no S2A C11A H112 109.43 . . . no C13A C12A H121 108.42 . . . no S2A C12A H122 108.52 . . . no S2A C12A H121 108.55 . . . no C13A C12A H122 108.40 . . . no H121 C12A H122 107.44 . . . no C13A C14A H14A 118.54 . . . no C15A C14A H14A 118.48 . . . no C14A C15A H15A 118.62 . . . no C16A C15A H15A 118.67 . . . no C15A C16A H16A 123.12 . . . no C17A C16A H16A 123.09 . . . no C18A C17A H17A 118.18 . . . no C16A C17A H17A 118.10 . . . no C13A C18A H18A 118.95 . . . no C17A C18A H18A 118.78 . . . no N4B C3B C11B 116.6(10) . . . yes N2B C3B C11B 116.8(10) . . . yes N2B C3B N4B 126.5(9) . . . yes C6B C5B C10B 121.0(10) . . . no Cl1B C6B C5B 117.0(8) . . . yes Cl1B C6B C7B 122.1(8) . . . yes C5B C6B C7B 120.9(11) . . . no S3B C7B C6B 124.5(8) . . . yes S3B C7B C8B 118.6(7) . . . yes C6B C7B C8B 116.9(9) . . . no C7B C8B C9B 120.7(8) . . . no S1B C9B C10B 118.0(6) . . . yes S1B C9B C8B 120.6(7) . . . yes C8B C9B C10B 121.4(8) . . . no C5B C10B C9B 119.0(8) . . . no N4B C10B C5B 119.2(9) . . . yes N4B C10B C9B 121.8(10) . . . yes S2B C11B C3B 112.6(8) . . . yes S2B C12B C13B 107.7(10) . . . yes C12B C13B C14B 124.0(12) . . . no C12B C13B C18B 119.4(13) . . . no C14B C13B C18B 116.4(11) . . . no C13B C14B C15B 123.9(14) . . . no C14B C15B C16B 118.2(16) . . . no C15B C16B C17B 120.4(14) . . . no C16B C17B C18B 120.1(15) . . . no C13B C18B C17B 120.9(15) . . . no C10B C5B H5B 119.60 . . . no C6B C5B H5B 119.36 . . . no C9B C8B H8B 119.84 . . . no C7B C8B H8B 119.51 . . . no S2B C11B H11B 109.21 . . . no S2B C11B H11A 109.01 . . . no H11A C11B H11B 107.88 . . . no C3B C11B H11A 108.88 . . . no C3B C11B H11B 109.14 . . . no C13B C12B H12C 110.13 . . . no C13B C12B H12D 110.12 . . . no H12C C12B H12D 108.58 . . . no S2B C12B H12C 110.10 . . . no S2B C12B H12D 110.23 . . . no C13B C14B H14B 118.10 . . . no C15B C14B H14B 117.97 . . . no C14B C15B H15B 120.98 . . . no C16B C15B H15B 120.82 . . . no C17B C16B H16B 119.94 . . . no C15B C16B H16B 119.71 . . . no C16B C17B H17B 119.83 . . . no C18B C17B H17B 120.04 . . . no C17B C18B H18B 119.63 . . . no C13B C18B H18B 119.49 . . . no loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1A S1A N2A C3A -144.1(8) . . . . no O2A S1A N2A C3A 90.5(8) . . . . no C9A S1A N2A C3A -26.4(9) . . . . no O1A S1A C9A C8A -43.6(11) . . . . no O1A S1A C9A C10A 145.3(8) . . . . no O2A S1A C9A C8A 83.9(10) . . . . no O2A S1A C9A C10A -87.2(8) . . . . no N2A S1A C9A C8A -161.4(9) . . . . no N2A S1A C9A C10A 27.5(9) . . . . no C12A S2A C11A C3A -66.0(8) . . . . no C11A S2A C12A C13A -70.1(10) . . . . no O3A S3A C7A C6A 171.1(7) . . . . no O3A S3A C7A C8A -8.1(10) . . . . no O4A S3A C7A C6A 42.2(9) . . . . no O4A S3A C7A C8A -137.0(8) . . . . no N3A S3A C7A C6A -75.5(9) . . . . no N3A S3A C7A C8A 105.3(9) . . . . no O1B S1B C9B C10B -143.3(8) . . . . no O2B S1B C9B C8B -88.4(8) . . . . no O1B S1B N2B C3B 145.8(8) . . . . no O1B S1B C9B C8B 39.3(9) . . . . no N2B S1B C9B C8B 157.4(8) . . . . no O2B S1B N2B C3B -87.9(8) . . . . no O2B S1B C9B C10B 89.1(9) . . . . no C9B S1B N2B C3B 26.4(9) . . . . no N2B S1B C9B C10B -25.1(10) . . . . no C11B S2B C12B C13B 168.1(10) . . . . no C12B S2B C11B C3B 73.5(11) . . . . no N3B S3B C7B C6B 73.2(10) . . . . no O3B S3B C7B C8B 12.7(9) . . . . no O4B S3B C7B C8B 139.5(7) . . . . no N3B S3B C7B C8B -103.5(8) . . . . no O4B S3B C7B C6B -43.7(10) . . . . no O3B S3B C7B C6B -170.6(9) . . . . no S1A N2A C3A N4A 12.7(16) . . . . no S1A N2A C3A C11A -172.4(7) . . . . no C10A N4A C3A N2A 6.0(18) . . . . no C10A N4A C3A C11A -168.9(9) . . . . no C3A N4A C10A C5A 172.3(11) . . . . no C3A N4A C10A C9A -4.2(15) . . . . no S1B N2B C3B C11B 164.7(8) . . . . no S1B N2B C3B N4B -10.6(15) . . . . no C3B N4B C10B C9B 13.7(16) . . . . no C10B N4B C3B C11B 171.7(9) . . . . no C3B N4B C10B C5B -166.9(11) . . . . no C10B N4B C3B N2B -13.0(17) . . . . no N4A C3A C11A S2A -58.2(11) . . . . no N2A C3A C11A S2A 126.4(10) . . . . no C10A C5A C6A C7A 2.6(15) . . . . no C6A C5A C10A N4A -174.9(9) . . . . no C10A C5A C6A Cl1A 178.9(8) . . . . no C6A C5A C10A C9A 1.4(16) . . . . no Cl1A C6A C7A S3A -0.8(12) . . . . no C5A C6A C7A S3A 175.3(8) . . . . no C5A C6A C7A C8A -5.5(14) . . . . no Cl1A C6A C7A C8A 178.4(8) . . . . no C6A C7A C8A C9A 4.4(16) . . . . no S3A C7A C8A C9A -176.4(9) . . . . no C7A C8A C9A C10A -0.4(16) . . . . no C7A C8A C9A S1A -171.6(8) . . . . no S1A C9A C10A C5A 169.1(9) . . . . no S1A C9A C10A N4A -14.5(12) . . . . no C8A C9A C10A C5A -2.6(15) . . . . no C8A C9A C10A N4A 173.8(9) . . . . no S2A C12A C13A C18A -54.9(16) . . . . no S2A C12A C13A C14A 125.5(13) . . . . no C14A C13A C18A C17A 1(2) . . . . no C18A C13A C14A C15A -3(2) . . . . no C12A C13A C18A C17A -178.3(13) . . . . no C12A C13A C14A C15A 176.4(15) . . . . no C13A C14A C15A C16A 4(3) . . . . no C14A C15A C16A C17A -3(2) . . . . no C15A C16A C17A C18A 1(2) . . . . no C16A C17A C18A C13A 0(2) . . . . no N4B C3B C11B S2B 93.3(10) . . . . no N2B C3B C11B S2B -82.4(13) . . . . no C10B C5B C6B C7B 0.0(18) . . . . no C10B C5B C6B Cl1B 179.5(10) . . . . no C6B C5B C10B C9B -2.9(18) . . . . no C6B C5B C10B N4B 177.6(11) . . . . no Cl1B C6B C7B S3B 4.2(14) . . . . no C5B C6B C7B C8B 0.5(16) . . . . no Cl1B C6B C7B C8B -179.1(8) . . . . no C5B C6B C7B S3B -176.3(9) . . . . no S3B C7B C8B C9B 179.0(7) . . . . no C6B C7B C8B C9B 2.0(14) . . . . no C7B C8B C9B S1B 172.4(7) . . . . no C7B C8B C9B C10B -5.0(15) . . . . no S1B C9B C10B C5B -172.1(9) . . . . no S1B C9B C10B N4B 7.4(15) . . . . no C8B C9B C10B N4B -175.1(10) . . . . no C8B C9B C10B C5B 5.4(17) . . . . no S2B C12B C13B C18B -88.1(16) . . . . no S2B C12B C13B C14B 96.3(14) . . . . no C12B C13B C18B C17B -176.6(15) . . . . no C12B C13B C14B C15B 177.9(15) . . . . no C18B C13B C14B C15B 2(2) . . . . no C14B C13B C18B C17B -1(2) . . . . no C13B C14B C15B C16B -3(3) . . . . no C14B C15B C16B C17B 2(3) . . . . no C15B C16B C17B C18B -1(3) . . . . no C16B C17B C18B C13B 0(3) . . . . no _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 69.98 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.576 _refine_diff_density_min -0.460 _refine_diff_density_rms 0.090 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # #D H A D - H H...A D...A D - H...A symm(A) # N3A H3A' O1WA 0.8800 2.1000 2.969(10) 173.00 . yes N3B H3C O1WB 0.8400 2.2100 2.936(10) 144.00 . yes N3B H3D O4B 0.8100 2.3300 2.997(13) 141.00 1_545 yes O1WA H1WA O1WA 0.8700 1.9400 2.768(12) 159.00 2_646 yes N4A H4A O2B 1.0800 2.0100 2.906(10) 138.00 . yes N4B H4B O2A 0.7800 2.2900 2.843(10) 128.00 1_455 yes O1WA H2WA Cl1A 0.7600 2.7200 3.427(7) 157.00 . yes O1WA H2WA O3B 0.7600 2.4700 2.864(9) 114.00 . yes O1WB H1WB O1WB 0.7500 2.1000 2.764(12) 147.00 2_556 yes O1WB H2WB O3A 0.9400 1.9600 2.874(9) 163.00 1_455 yes C8A H8A O3A 0.9300 2.3700 2.809(11) 109.00 . yes C8B H8B O3B 0.9300 2.4500 2.847(11) 106.00 . yes C11A H112 O2B 0.9700 2.4500 3.348(14) 154.00 1_565 yes C14B H14B S2A 0.9300 2.8200 3.733(15) 166.00 . yes ################### END #########################